Your total trip with all stops is around 980 miles / 1570 km, taking roughly 15.5 hours for the whole trip. If you want to see every small town along the way, you can get a full list of cities between CHS and MDW.
Start from Charleston International Airport.
Charlotte, North Carolina is stopping point #1 after driving about 200 miles (320 km) or 3 hours.
Knoxville, Tennessee is stopping point #2 after driving about 230 miles (370 km) or 4 hours. Your total trip so far is about 430 miles or 690 km over roughly 7 hours of driving.
Lexington-Fayette, Kentucky is stopping point #3 after driving about 170 miles (270 km) or 2.5 hours. Your total trip so far is about 600 miles or 970 km over roughly 9.5 hours of driving.
Indianapolis, Indiana is stopping point #4 after driving about 190 miles (300 km) or 3 hours. Your total trip so far is about 790 miles or 1270 km over roughly 12.5 hours of driving.
Finally, Chicago Midway International Airport is your destination after driving about 190 miles (300 km) or 3 hours. Your total trip with all stops is around 980 miles or 1570 km, taking roughly 15.5 hours for the whole trip.
Travelmath helps you figure out where to stop when planning a long road trip from one location to another. The best stopping point for an overnight hotel stay or a break from driving often depends on how far or how long you want to drive before pausing to rest. You can find the closest city to your stopping point to look for hotels, or explore other cities and towns along the route. Use this as a road trip planner when you're driving cross-country or mapping a route with multiple stops.